rac-(S*)-5-(2,6-dimethoxyphenyl)-3-methylene-1-(4-(trifluoromethoxy)benzyl)pyrrolidin-2-one → 5-(2,6-Dimethoxyphenyl)-3-methyl-1-(4-(trifluoromethoxy)benzyl)pyrrolidin-2-one

Participants

Reaction Steps

A mixture of rac-(S*)-5-(2,6-dimethoxyphenyl)-3-methylene-1-(4-(trifluoromethoxy)-benzyl)pyrrolidin-2-one (310 mg; 0.76 mmol), and 10% Pd(C) (62 mg; 20% in mass) in anh. MeOH (3 ml) was stirred at rt, under hydrogen atmosphere (1 atm), for 60 h. Filtration over a pad of celite, concentration to dryness under reduced pressure, and subsequent purification by FC (DCM/MeOH=30/1) afforded rac-(3S*,5S*)-5-(2,6-dimethoxyphenyl)-3-methyl-1-(4-(trifluoromethoxy)-benzyl)pyrrolidin-2-one as an orange oil. LC-MS (conditions A): tR=0.94 min.; [M+H]+: 410.27 g/mol.

Provenance & Evidence